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Usage

Uses

Used in Pharmaceutical Synthesis:
(Z)-2-Buten-2-ylboronic acid pinacol ester is used as a key intermediate for the synthesis of complex organic molecules, particularly in the pharmaceutical industry. Its role in forming carbon-carbon bonds is crucial for the development of new drugs and medicinal compounds.
Used in Agrochemical Synthesis:
In the agrochemical industry, (Z)-2-Buten-2-ylboronic acid pinacol ester is utilized as a building block for the creation of various agrochemicals. Its ability to form carbon-carbon bonds aids in the synthesis of molecules with potential applications in agriculture, such as pesticides and fertilizers.
Used in Material Science:
(Z)-2-Buten-2-ylboronic acid pinacol ester is employed as a versatile tool in the field of material science. Its use in forming diverse chemical structures contributes to the development of new materials and chemical products with potential applications in various industries.
Used in Organic Synthesis Research:
As a reagent in organic synthesis, (Z)-2-Buten-2-ylboronic acid pinacol ester is also used in academic and research settings. Its stability and solubility in organic solvents make it an attractive compound for synthetic chemists working on the development of novel materials and chemical processes.

Upstream product

• 503-17-3 dimethylacetylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 177949-90-5 4,4,5,5-tetramethyl-2-(oct-1-en-2-yl)-1,3,2-dioxaborolane 
• 75851-67-1 4,4,5,5-tetramethyl-2-(1-methyl-2-propenyl)-1,3,2-dioxaborolane 

Downstream Products

• 1622201-99-3 (2S,3E)-3-methyl-2-phenyl-2-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolanyl)pent-3-ene 
• 1622202-01-0 (2E,4S)-3-methyl-4-phenyl-4-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolanyl)hex-2-ene 

Relevant academic research and scientific papers

Pincer Iron Hydride Complexes for Alkene Isomerization: Catalytic Approach to Trisubstituted (Z)-Alkenyl Boronates

An iron dichloride complex [Fe]Cl2 supported by a pincer phosphine-pyridine-imidazoline (PNNimid) ligand {[Fe]Cl2 = (PNNimid)FeCl2}, upon activation with NaHBEt3, catalyzes the isomerization of 1,1-disubstituted alkenyl boronates to synthetically valuable

Ru-catalyzed isomerization of ω-alkenylboronates towards stereoselective synthesis of vinylboronates with subsequent: In situ functionalization

The stereoselective preparation of synthetically versatile vinylboronates from ω-alkenylboronates is achieved through a ruthenium-catalyzed isomerization reaction. A variety of di- A nd trisubstituted vinylboronates were conveniently produced and could be

Tris(2,4,6-trifluorophenyl)borane: An Efficient Hydroboration Catalyst

The metal-free catalyst tris(2,4,6-trifluorophenyl)borane has demonstrated its extensive applications in the 1,2-hydroboration of numerous unsaturated reagents, namely alkynes, aldehydes and imines, consisting of a wide array of electron-withdrawing and donating functionalities. A range of over 50 borylated products are reported, with many reactions proceeding with low catalyst loading under ambient conditions. These pinacol boronate esters, in the case of aldehydes and imines, can be readily hydrolyzed to leave the respective alcohol and amine, whereas alkynyl substrates result in vinyl boranes. This is of great synthetic use to the organic chemist.

Highly diastereo- and enantioselective allylboration of aldehydes using α-substituted allyl/crotyl pinacol boronic esters via in situ generated borinic esters

Readily available, α-substituted allyl/crotyl pinacol boronic esters often give low E/Z selectivity (with Z favored) in reactions with aldehydes. We found that addition of nBuLi to the pinacol boronic ester followed by trapping of the alkoxide with TFAA leads to an intermediate allyl borinic ester which undergoes allylboration with very high E selectivity. The substrate scope includes primary to tertiary alkyl α-substituents, crotyl substrates, and the previously unreported β-methallyl pinacol boronic esters. The latter give very high Z selectivity under standard conditions which is completely reversed to high E selectivity under the new conditions. Monitoring the reaction by 11B NMR confirmed that the reaction proceeds through a borinic ester intermediate.